


Five Reasons Sam Knows Chloe Is Perfect For Dean

by sarcastic_fina



Series: Five Times (Chloe/Dean) [3]
Category: Smallville, Supernatural
Genre: F/M
Language: English
Status: Completed
Published: 2008-09-17
Updated: 2008-10-03
Packaged: 2018-09-13 13:51:51
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 7,994
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9126553
Author URL: https://archiveofourown.org/users/sarcastic_fina/pseuds/sarcastic_fina
Summary: Sam Winchester has five reasons that prove Chloe Sullivan is the perfect woman for his brother Dean.





	1. Chapter 1

**Author's Note:**

> Please keep in mind this story was originally written in **2008** and my writing style and ability has changed and grown. I'm moving this story here as I'm going to be deleting my LJ soon.

**1**. _She Doesn't Put Up With His Crap_

The music was loud; enough to break eardrums at any second. Had been for the last six days while Dean worked out whatever was bugging him this time. Sam was sick and tired of it but every time he brought it up, he was shut down and ignored in favor of work. If he had to listen to much more of this though, he was either jumping out of the Impala while it was still moving or something even _more_ dramatic could be in the near future.

Reaching over, Chloe did the unthinkable. She turned it _off_. With a scowl, Dean glared at her.

"I'll make this easy," she said, leveling him with a stare. "You either tell us what crawled up your ass, Winchester, or I put Britney on!"

His jaw clenched and he eyed the radio before turning back to the road.

Chloe began digging around in her bag. "Hit Me Baby One More Time or Oops, I Did It Again?" she asked, lifting a brow.

Dean shook his head. "Blasphemy," he muttered.

With a sigh, she leaned forward, resting her chin on his shoulder. "I've put up with way too much Zeppelin and Metallica for your little hissy fit, Dean. So either spill your guts or put up with ear bleeding pop music." She waited, not moving or saying anything more.

Sam could see his jaw twitch and wondered if maybe he should warn Chloe about Dean's short fuse. But then, she'd been around awhile now and she knew Dean, better than probably any woman before her. The fact that he wasn't immediately shouting or pushing her away said something in itself. Sam held his breath, waiting for something, anything to happen.

When Chloe reached forward, Britney Spears tape in hand, Dean turned the car swiftly to the side and brought it to a humming halt. He gripped the steering wheel tightly, his knuckles turning white. She sat back, knowingly, just waiting for him to finally spill what was on his mind. And Sam knew then, even before his brother finally said what had been on his mind the last week, that Chloe Sullivan was going to be one of those people; one of those women in Dean's life that left such a big impression, she was never forgotten. And the fact that Dean listened at all, that he didn't just bite her head off and throw her tape out the window, meant that his brother already knew that too.

When all was said and done and they were back to driving, this time without the earsplitting metal-rock and thankfully not the sugar-sweet pop music either, Dean turned in his seat to eye the blonde in the back. "You ever put Spears in my stereo and you're riding in the trunk."

She simply grinned.

Dean tried to hide his amused smirk before turning back toward the road.

Sam put a hand over his mouth and stared out the window so his brother wouldn't see his knowing smile. Their family road trip just got way more interesting; he was suddenly happy that his brother had picked Chloe up in the bar and invited her along on their unusual journey. He had a feeling things were going to be taking a different route than Dean ever expected and Sam was happy for it.


	2. Chapter 2

**Summary for the Chapter:**

> Sam Winchester has five reasons that prove Chloe Sullivan is the perfect woman for his brother Dean.

**2**. _He actually gets jealous_

"Look at him... Stupid Don Juan reject," Dean muttered, lifting his beer to his mouth once more.

Sam cocked an amused brow at his brother before looking back over at Chloe who was currently hustling some guy in pool and putting on the charm so he wouldn't catch on to her ploy. "It's just a game, Dean.

"I know," he replied stiffly, shrugging. "Just don't think it's smart having her pull in the money. All these drunk, groping apes, ready to drown her in their drool."

He smothered his laugh. "Uh... Getting jealous?"

"What? No." He snorted. "Every chick in here's been eyeing me up."

"Yeah..." Sam looked around at the few women remaining, either too drunk to see straight or nowhere near Dean's already low standards. "Quite the pick you got there."

"Shut up," he muttered, staring at Chloe still, watching as the guy fumbled behind her, rubbing his crotch against her backside and acting as though it was a complete accident.

It was clear to everybody but the guy behind her that Chloe was disgusted, but Dean still frowned, glaring at the guy. "You know... She came in here with us, so for all he knows, she's one of ours... Least he could do was check!"

"She's not though." Sam stared at him. "Chloe's single and therefore-"

"Yeah but he doesn't know that," he ranted. "She walked in with us; she could be leaving with us. But does that stop him from feeling up her ass? No! No, he's all over her ass."

"Uh, Dean-"

"And look at her, just soaking it all in." She laughed across the room but even Sam could hear it was forced.

"Maybe you should-"

"Did you see that?" Dean interrupted, crossing his arms over his chest.

Sam's brow furrowed, glancing over at the two. The guy was standing a little close, sipping his beer and peering down at Chloe as she bent forward to take her shot, purposely showing off a little cleavage. "See what?" he asked.

"The casual boob touch..." He nodded, eyes thinned. "Idiot thinks he's gonna get lucky."

He sighed, rolling his eyes. "Yeah and if he stays thinking that he'll continue to suck at pool and Chloe can pay for our room tonight," Sam reminded, shaking his head.

"I swear if he touches her one more time..."

"Dean!" He shook his head. "I'm not spending another night in the Impala because you can't admit-"

"I'll be right back." He was up and off his stool before his brother could finish and Sam sighed, watching as Dean crossed the room, boots clomping.

As Chloe looked up, her already stiff smile faded as she lifted a warning brow at Dean. He shrugged his shoulder like he didn't know what she was trying to stop him from doing and then rounded the table. Sam didn't have to be there and hear what was being said to know what was happening. Dean's arm slid around Chloe's waist and because she wasn't willing to get into it with Dean and likely loose any winnings, she leaned into him too, her head naturally falling to his shoulder. Dean said something down to her and then smirked up at the guy she'd been scamming as if to say, "Better luck next time, chump, this one's mine."

Sam caught Chloe's annoyed eyes across the room. She pursed her lips and a moment later when he noticed Dean wince, he knew Chloe had pinched him. To get back at her, he slapped her butt and then motioned for her to wrap up the game. He walked back across the room and grabbed up his beer, now looking quite smug as he sat back down.

"Feel better?" Sam asked, shaking his head.

"Much." He nodded.

"One of these days, you know... She's not going to put up with that."

He grinned, nodding. "Yeah, not tonight though. She'll be done in five and then we can get some sleep." He yawned, leaning back on the bar with his elbows.

"Yeah Dean..." He scoffed. "You interrupted them because you were tired."

Dean glared. "What other reason is there?"

Sam shook his head. "I could think of a few."

"Yeah, whatever." He sipped his beer and waited for Chloe to come on over, hips swaying and money in hand. She slapped it down against Dean's chest with a frown.

"Let's go, Caveman," she told him before leaving the bar for the Impala.

With a sigh, Dean followed after her. "I wanna stop for something to eat first."

"Suck it up," she called back.

"You suck it up," he muttered lamely.

Rolling his eyes, Sam threw down some money for their beers and headed out after them. At least she managed to finish the game this time; at the last Dean couldn't put up with it any longer and interrupted, nearly dragging her away in the process so they were stuck sleeping in the Impala, again. He spent half the night listening to them argue over why he was being a jackass about her doing the scamming every once in awhile. Sam was ready to climb out and sleep on the highway when Dean muttered his version of an apology and they all finally got some sleep. But if it happened again, he wasn't going to hold back. He was going to make sure his brother knew that everybody was well aware he had feelings for their snarky blonde companion and hopefully _that_ would shut Dean up, for once.


	3. Chapter 3

**Summary for the Chapter:**

> Sam Winchester has five reasons that prove Chloe Sullivan is the perfect woman for his brother Dean.

**3**. _She Encourages His Hunting, Only If He Wants To_

The Motel room door slammed as Dean came stomping inside, covered head to toe in ectoplasm, mud and blood. He grumbled under his breath, his sawed off hanging from his hand as he collapsed into a chair across from them. Chloe merely glanced up at him, half-smiled and then turned her attention back to her laptop.

"W-What happened to _you_?" Sam asked, stifling his laughter and staring at his brother with large eyes.

He glared. "Hunting," he said, voice so dark, it sounded like he was cursing.

"What was it?" he wondered.

"Does it matter?" he asked grumpily, slouching in his chair further. "I friggin' hate this job. Sick and tired of this crap. Ruined my leather jacket." He glowered.

"I really liked that jacket," Chloe said with a grin.

"Me too," Dean muttered through grit teeth.

"I didn't know you were on a job or I would've come." He glanced at Chloe, who simply shrugged.

"He wanted to do this one himself," she said, lifting her mug of coffee to her mouth, a brow quirked as if she'd proven a point somehow.

"It was supposed to be easy. A quick in and out, back before we hit the road thing."

"And then...?"

Dean threw his arms out to the side to emphasize the mess all over him.

"Did you win?" Sam wondered, half-smiling.

"Course I won," he replied, sounding offended that his brother even had to ask.

Chloe sniggered.

Dean frowned. "Not the point, though." He crossed his arms, looking halfway to pouting. "I'm sick of this crap."

"Quit," Chloe said, never pausing in her typing.

He snorted. "Yeah... Right."

"You don't like it, there's no health plan, and you smell... Quit." She shrugged.

"I can't just..." He pursed his lips, shaking his head before staring out in contemplation. "I'm a good mechanic... They were looking for one at the shop a few blocks over."

Sam stared at him, wide-eyed. Was he actually considering...? But hunting was his life! He'd probably drive himself up the wall, always wondering if people had died because he wasn't there, because he knew about the things that go bump in the night but didn't do anything about it... And why was Chloe so _whatever_ about it? She'd been on the road with them almost a year now, she knew their entire history, good and bad, she had to know Dean well enough that he was a born and bred hunter!

"Yeah. I'm doin' it." Dean slapped the table with his hand. "I quit."

"Good. Now shower," Chloe said, brows furrowed as she typed away.

Dean sniffed himself before making a face and nodding, standing up from the chair as he moved toward the bathroom.

"Uh, Chloe? Not that I don't agree that the job has its downsides, but... Dean is... well, _Dean,_ and..."

"Just trust me, Sam," she said, giving him a mysterious smile.

Two weeks later, it all made sense.

The Motel room door slammed and Sam looked up from the newspaper he'd been looking through, red felt in hand, four obits already circled.

"I friggin' hate this crap," Dean exclaimed, walking in covered in the usual engine oil. He slumped down into a chair. "I hate people. All they do is whine about stupid shit." He glowered. "I have to pay taxes, I have to take my kid's to soccer, my husband's cheating on me so I'll sleep with his mechanic," he imitated, rolling her eyes.

"You sleep with her?" Chloe asked casually as she closed her laptop and joined them at the small table.

He frowned at her. "No."

She smothered a smile. "Why not? Too old, too young, or was it just the wedding band that bothered you?"

He lifted a brow. "I don't do married chicks and..." He shrugged. "Didn't feel like it."

" _You_ didn't feel like having sex?" She chuckled, shaking her head as leaned back in her chair. "Okay, continue whining."

"I'm not whining, I'm... venting."

She rolled her eyes.

Glaring at her, he turned back to Sam. "The job's fine... It's the people that suck."

Sam sighed. "Well, maybe ask your boss if you can just work on the cars and not have any actual interaction with the customers."

"Tried that... They come looking for their cars." He shook his head. "And then they stand there while I'm working and tell me about their boring lives and how much they have to deal with and all I wanna do is throw a wrench at them." His eyes widened with irritation. "They think _they_ got it bad? Hell, I'd like to see them take on a full nest of vampires and _then_ they can bitch."

"You didn't _do_ that, did you?" Sam's brows furrowed.

"'Course not... Probably wouldn't get paid." He ran a hand through his hair. "But I'm tired of this... People are idiots. Crazy, screwed up, idiots."

"So quit. Go back to hunting," Chloe said, lifting a shoulder.

"I just quit hunting, I can't just go back..." He crossed his arms, glowering. "And it doesn't pay as good."

"It doesn't pay at all," she reminded, amused. "But the only people you have to deal with are the ones with real problems."

He nodded, frowning thoughtfully.

"Plus you get to drive the Impala ninety percent of the day."

He grinned. "I miss her... We don't spend enough time together."

Chloe rolled her eyes.

Dean slapped the table decidedly. "I'm quitting. Picking up my sawed off again." He looked over at Sam. "Anything good in the obits?"

Sam sighed. "A few mysterious deaths..."

"Awesome." Dean stood up. "I'm taking a shower. Get your crap together. We're outta here in a half hour." He walked off and shut the door behind him.

"You knew that was coming, didn't you?" Sam asked, looking toward Chloe knowingly.

She smiled. "If he wants to hunt, he should hunt. And if he doesn't..." She shrugged. "What's important is that he knows that he can do either. That his life isn't set for him." She stood up, taking her laptop to her bag to put it away.

Sam grinned. Yet another reason why he knew Chloe was right for his brother. She understood Dean better than he understood himself, and she supported him in any life he chose. He shook his head before standing up to get his things together. He was happy they were getting back on the road. He was sick and tired of this little town and sitting idle. He was glad Dean was back to hunting form; it was how he was meant to be.


	4. Chapter 4

**Summary for the Chapter:**

> Sam Winchester has five reasons that prove Chloe Sullivan is the perfect woman for his brother Dean.

**4**. _She Embraces Sam/Dean Time_

They were in a bar; one of thousands they'd been to before. Half the patrons were drunk, the others on their way. There were a few pool tables set up, a game of poker being played in the corner, a jukebox playing some oldies, and a few couples dancing sloppily. He, Dean, and Chloe all shared a table, a few empty bottles between them. They were relaxing after a long hunt and after this it'd be sleeping in at the Motel before they were back on the road, searching for the next job. Chloe hung around an hour before claiming she was tired. Sam could see she was wired and she'd glanced at the dance floor a few times before her eyes wandered over to Dean. He wouldn't go, but she'd managed to pull Sam up for a couple fast songs earlier.

"I'm going to head back to the Motel and get some sleep," she said, standing up from her chair.

Dean reached for his jacket but stopped as she put her hand on his. "You guys should stay, enjoy your night."

Sam grinned. She did this a lot; encouraged them to hang out without her. She didn't want to impose on them and she claimed their brotherly charm is what attracted her to "road tripping" with them in the first place.

"You sure? I can drive you back," Dean offered, brow furrowed.

She chuckled. "Dean, it's around the corner. If any big bad's come for me, I'm sure I got it covered."

He sat back in his chair, still not entirely certain. Leaning down, she kissed his cheek. "Have another on me, huh?" she said before lifting his beer and finishing off the last couple swigs. She dropped the empty bottle by his hand and rounded the table to Sam. "Try to keep the drunken singing to a minimum when you guys get back," she teased, kissing his cheek too. She squeezed his shoulder before walking toward the door.

"What was that?" Dean asked, lifting a skeptical brow at him.

Sam rolled his eyes. "I don't have a thing for Chloe, Dean. And trust me, her feelings are completely platonic."

He shrugged. "Whatever. She's a grown woman... If you want her..." He turned his eyes off and motioned for another couple beers.

"You'd have my head on a pike." He lifted his brows for emphasis.

He leaned forward, arms resting on the table. "Only if you broke her heart." He half-smiled but it was stiff with warning.

"You don't have to pretend, you know... I figured it out from the beginning."

"Yeah?" Dean nodded his thanks to the bartender before cracking open another beer and taking a swig. "And what'd you figure out?" He lifted a brow.

"That you love her... That you're willing to do just about anything to have her." He shrugged, playing with the label on his beer absently. "I get it, man... Chloe's..."

"A friend and a hunter," Dean told him sternly. "Meaning she's the last person I need to be hooking up with."

"But that's just it, right?" Sam smiled rather sadly. "You don't wanna just hook up with her."

Dean snorted, shaking his head. "You don't know what I want... I think you should lay off the beer, Sammy."

He leaned forward. "I'm sober enough." He stared at him long and hard. "How drunk do I have to get you before you're honest with me?"

"About Chloe?" He smirked. "Pretty damn drunk."

Sam grinned. "Done."

Three hours later, Sam sat laughing; about what, he couldn't remember.

Shaking his head and recovering from his own laughter, Dean leaned back in his chair with a content sigh. "What were we talking about?"

Sam shrugged. "Can't remember."

Taking a drink of his beer, Dean nodded. "Chloe's been in the bathroom forever."

"Chloe's back at the motel."

Dean turned his head up, brow furrowed. "Oh yeah..."

Sam slapped his shoulder. "I shouldn't've played drink for drink with you... I 's supposed to stay sober to interrogate you."

He snorted. "I know... That's why I suggested it."

Shaking his head, Sam rubbed his forehead. "I just don't... I don't _get it_..." He sighed with drunken irritation. "You love her and she... She is _awesome_. So why don't you guys just..." He clapped his hands together and held them up to show him. "You know?"

"You're so drunk," Dean laughed.

"I am." He nodded. "But I'm also right."

"You usually are."

"Uh huh," he agreed, drinking the rest of his beer before lifting his hand for another. "She does this, you know... Leaves us here for Sam/Dean time."

"What the hell's that?" Dean frowned.

"We're s'posed to bond and crap..." He stared at him blearily. "It's how I know she loves you... She doesn't keep you for herself."

"She shares me?" He grinned goofily. "That's sexy."

"Ew." Sam shook his head. "You haven't even looked at another girl for like... a lot of cities."

He nodded. "She just got into my head, you know? And ev'ry time another woman came onto me, I just sort've..." He waved his hand around. "Didn't want them."

"That's weird."

Dean nodded, eyes thinned. "It's like she put a spell on me... You think she's a witch?"

"You're even drunker than I thought," Sam muttered, shaking his head drowsily. "What I meant was she like... She gets us... She's not trying to push me away, you know? She like... She knows we're really close and she doesn't... She doesn't want that to change." He shook his head, frowning. "Other girls would... Other girls would want you all to themselves... If you ever had any girls longer than a night."

"Hey I could have ‘em if I wanted ‘em," Dean declared.

"Then why don't you have Chloe?"

"Cause she's... _Chloe_!"

"That doesn't explain any-"

"No, I mean... Chloe!" He grinned, waving.

Sam looked up, grinning woozily at the blonde smiling down at them, shaking her head.

"You two are plastered."

They laughed, leaning back and nodding.

"All right, come on boys," she sighed. She shook her head as the bartender came over with another few beers, but Dean nodded.

He reached over and grabbed her hand, dragging her over until she fell into his lap. He put his head on her shoulder. "You know what you are? You are _awesome_. Tell her Sammy."

Sam nodded, grinning in his drunken haze. "Totally awesome."

"No arguments here," she assured, lips curled with a smile. "Let's see if you're both singing the same tune tomorrow morning though, huh?"

"If we stay up all night drinking, there's no tomorrow morning to worry about," Dean told her in his most logical voice.

She patted his cheek. "Yeah... Let's get you back to the motel and into bed, okay?"

"You gonna join me?" He smirked at her.

She lifted a brow. "You wouldn't know what to do with me." She stood up from his lap and took his hand, helping him up before she moved over to help Sam out of his chair. She shook her head at the bartender as Dean tried to grab another beer and then dug into his jeans for a few bills to pay off their tab. "Come on, you two," she said, hooking her arms with them and beginning the trek back to the motel.

"We should sing," Sam said, sighing as he shuffled side to side.

"No, you really shouldn't," Chloe told him, shaking her head.

"You like it when we sing." Dean leaned against her, resting his chin on her head, burying his nose in her hair and inhaling deeply. "You like my voice."

"I put up with your voice, there's a difference." She rolled her eyes.

"Liar."

She smiled up at him. "You think you'll remember this tomorrow?"

He snorted. "No."

"Good. Then your voice is beautiful."

He grinned widely. "See? What'd I tell ya?"

"I don't know, do you?" she teased.

His expression scrunched up, brows furrowed. "Huh?"

"Exactly."

"You're mean to drunk people," Sam told her, shaking his head.

She shrugged unapologetically. "It's your own fault."

"It's really _yours_... If you and Dean would just..." He clapped his hands together like he had earlier in hopes that she'd get it.

Her eyes thinned as she shook her head slowly. "Play pattie cake...?"

He glowered. "No... You gotta... You know?"

"No. I really don't."

"You do too... You're just pretending you don't ‘cause then you'd have to admit that you love him too and then he'd have to admit that he loves you and then you guys will all be in love and I'll just _not_..." He pouted. "But I want that... Not the me not loving part but the you two loving part because you two are like... like yeah. Okay? You get him and he gets you and you get each other."

"And apparently when drunk you get completely ineloquent."

He snorted. "Whatever."

Her brows lifted with emphasis. "Point proven."

They stumbled around the corner with Chloe trying to keep their two heavy bodies from colliding with various objects before she finally stopped in front of the motel room door and unlocked it. Kicking his shoes off, Sam yanked his shirt up over his head and then fell onto his bed, curling up in a ball and stuffing his arms under his head for a pillow. "'m so tired..." he whined.

"Then go to sleep," Chloe told him, locking the doors and then checking the windows. She replenished the salt barrier and then found Dean struggling to get his shirt off. With a small laugh, she helped him peel it away and then directed him toward his bed. "Did you guys at least have fun?"

"Yeah..." Sam grinned, his eyes closed. "You do it on purpose, don't you? You leave us so we can have Sam/Dean time."

"Not what I usually call it, but hey, to each their own." She shrugged, sitting down on the end of her bed. "You guys should have some time to yourselves, without me hanging around as a shadow."

"We like you," Sam assured. "One of us more than the other."

She laughed. "Smooth."

He grinned.

"'m coooold," Dean called out, voice muffled as he laid face down.

"Then get under the blanket," Chloe replied exasperated.

"Don' wanna move."

Sam could hear some shuffling and then Dean sighed so he knew Chloe had given him a hand.

"We played pool and poker and had a drinking contest," Sam listed, rolling onto his side. "And we forgot all about hunting and death and all the crap that follows us everywhere. It was... great."

Chloe smiled. "Good. I'm glad."

"Thanks Chlo," he sighed, eyes fluttering closed as he relaxed into the bed once more.

"For what?"

He shrugged, sighing tiredly. "For not being like other women... For understanding us."

He could tell the lights had been shut off and knew she was getting into her bed. "Yeah, well... I don't think just any woman could fit in with you two."

Sam smiled agreeably. He'd have one killer hangover the next morning, but it was yet another night that had taught him a thing or two about the spunky blonde that had joined their exclusive hunting team. While she might one day win the heart of his brother and they could potentially have the happy ending, she knew them well enough that she'd never try and separate them for any reason. She wasn't out to come between them but instead supported their strong brotherhood and went out of her way to make sure it stayed in tact. If Sam had any say in Dean's love life, he'd have to say he just struck gold. Too bad his brother was too stubborn to figure it out.


	5. Chapter 5

**Summary for the Chapter:**

> Sam Winchester has five reasons that prove Chloe Sullivan is the perfect woman for his brother Dean.

**5**. _She Gets Dean To Say I Love You_

In his opinion, it took far too long, but if he were to ask Dean, he'd just say Sam was seeing things that weren't there yet. He refused to admit that he'd been pining after Chloe for months. Given they share a hotel room it was hard to hide the relationship from in _any_ capacity. So when he woke up in the middle of the night to them _actually_ arguing while they went at it in the bed across from him, he was half happy and half disgusted. That was just _not_ something he needed to hear.

_"You're gonna wake him up!"_

_"_ I'm _going to wake him?" Dean snorted. "You're the one screaming, sweetheart."_

_"I was not screaming... I was panting loudly." Even without seeing her, Sam knew she was rolling her eyes. "Shut up. That's so not the point right now. It is all kinds of wrong that we're doing this with Sam in the same room. What if he wakes up?"_

_"You know what's all kinds of wrong?" He just knew Dean's brow was lifted. "That you're talkin' about my brother while I'm inside of you."_

_"Is now_ really _the time to be jealous? I told you, Sam is like my best friend."_

_He couldn't help but grin, even if he was listening in on a private conversation and fully aware that his brother and best friend were currently..._ interlocked _._

_"Can we_ not _talk about Sam, right now?"_

_"It's hard not to when he's right-Oh! Oh, God..."_

_"Mm... That's better..."_

_And that was when he did his best to muffle Chloe's screaming/"loud panting" with the pillow over his head and fell into an uncomfortable sleep, wishing he could forget everything he just heard._

Besides Dean's advances no longer being ignored, not a lot changed in the dynamics of the team. They only had to pay for two beds again, which Dean said shouldn't have _ever_ been an issue since he offered up half of his bed to Chloe from the beginning. And while he had to put up with their public displays of affection, he was still too happy for them to really care. The biggest and most noticeable change was in Dean; he was still the cocky, confident, devil-may-care guy he'd always been, but he wasn't as dark as he'd been becoming. While he didn't sit around and cry all day long, spilling his every deep, dark secret, he was more honest with Chloe than he'd probably ever been with anybody but Sam. And he didn't fake his happiness, it was clear that he was actually content now that he and Chloe had gotten past the denial in terms of what they shared, he was free to enjoy an actual relationship with her.

It wasn't always easy given there was a constant third party at their sides and maybe if it'd been anybody _but_ Chloe, that would've caused serious issues in the relationship, but she welcomed Sam along with Dean. And if Dean hinted every once in awhile that he should really give Sarah Blake a call, well he was pretty sure it wasn't so much a "Go away!" as a "Find what I got, little brother." And there was more than once where his fingers hovered over the speed dial of his cell phone, wanting to call and see what she was doing, maybe take a trip out to see her and leave Dean and Chloe to their own quality time weekend. But work was never that forgiving and it was a long time before the idea of a vacation ever really had a chance.

Eleven months, three weeks and four days... That was how long it took for him to say _it_. He wasn't counting, he just happened to look it up after marking what day Dean finally gave in and kissed Chloe for all she was worth, effectively starting their relationship. Even if he didn't know about it until later that very uncomfortable night. And now they'd been together almost a year, which in Sam's books meant that what they had was serious and real and meant to last. Because Dean just didn't do the relationship thing, not unless he really meant it. But he hadn't said _those_ words yet. They were implied, everybody knew that he did, but he never _said_ them.

So while Sam was sitting at the table, searching through his computer for any weird occurrence that might lead them to their next case he was in for a big surprise.

Chloe was sprawled out on the bed, a book in one hand and the other running through Dean's hair as he rested his head in her lap, flipping through the channels on the TV. This was normal; this was a regular night between the three of them. The only change was when Dean gave him the hinting eyebrow raise that meant he should go hang out at some lame diner for a few hours while he cuddled up with Chloe in less clothing. Sam didn't mind as long as Dean remembered to give him his laptop before he shoved him out the Motel door. It was better than waking up to hear them going at it and not bothering with any worry over the volume, either.

But since he hadn't been given Dean's patented "shoo" look, he was free to kick off his boots and sit back in the chair, browsing web pages and online blogs or newspapers for any kind of weird activity. Currently, Chloe was deep into one of her romance novels, which she said were often made of so much fantasy, they got her mind off the darkness around her. Dean occasionally stole these books from her, teasing her as he read out sex scenes that were far too cheesy before then shooing Sam out of the room. His other form of teasing was to encourage her to read them aloud so he could mock it. She let him, shook her head and returned to the book.

"What's Don Juan sayin' now?" he asked abruptly, turning off the TV. He rolled over so he was facing her, his fingers playing with the them of her shirt, an old Zeppelin tee that Dean kept from what must've been his early teens, because there was no way he would've fit into it in the last decade or two.

Not bothering to question it, she began reading aloud, even drawing Sam from his task with her low voice, " _He stood, ram-rod straight, glaring down at her as his broad, heaving chest seemed to remove all space between them. His eyes, dark as night, pierced her soul and left her bare in every sense of the word._

_"What do you want from me?" he growled, as if the mere question itself had angered him, as if her wanting anything was against protocol._

_"What can you give?" she replied, tone steady while her hands shook violently at her hips._

_"You're playing with fire... I'm not the kinda man you need."_

_She swallowed tightly. She knew that. She should be back home, wrangling up someone who would give her everything and more, worship the very dirt she walked on, and thank his lucky stars that he'd ever found her. But here she was, staring up at a brooding man who might as well have sold his soul by now, he was so jaded by the world itself. "You're the man I_ want _. And I get what I want..."_

_His eyes thinned, a sneer of stubbornness on his full lips. "What makes you so sure I want you?"_

_She forced a laugh from her throat, hoped he hadn't realized it was so brittle. "Tell me different."_

_He didn't reply which she couldn't find reason to mind when he buried his large hand in her hair, drew her up against his chest and possessed her mouth just as strongly as he did his gun or his badge. Just as quick and deep as he showed day in and day out as he hunted for justice and found it in the depths of hell itself. And she didn't stop him, prayed he never drew away. Fuck air, she'd gladly die so long as this never ended, so long as she never had to leave his arms or question her morality and the decisions she'd made. Yes, he wasn't the type of good man her mother had always wanted for her and her dad would take one look at him and ask her if she lost her mind. But he was a good, loving man, who would do nothing but keep her safe and love her to the very depths of his dark, jaded soul. And she wasn't willing to let herself search for another, not when she knew that where she was meant to be was where she currently was. In the arms of-"_

"I love you."

Sam had grown so interested in the reading (not that he'd _ever_ admit it) that Dean's voice jarred him. He turned his head, eyes wide, stared at the back of his brother's head as if he expected it to sprout something unusual.

Chloe stared down at him, closing her book and dropping it to the bed. "For some reason I always imagined I'd be feeding you pie when you said that..."

He laughed, but the tone was off... as if he was nervous by his declaration and was only chuckling to ease the awkwardness.

It was then that Sam realized that while Dean had never said _those_ words and it was something that continued to confuse him, he hadn't even taken in the fact that Chloe hadn't said it either. He assumed that it was just her way of letting him know there was no pressure. That she didn't expect big declarations or the promise of a white picket fence. But it was now that those words pretty much _had_ to be returned, because not saying them was sure to ruin whatever it was they had. Sam held his breath, briefly telling himself he was being a total girl. Odd that it was _Dean's_ voice that said those words in his head.

She smiled at him, her fingers lightly stroking his temple. "Do you want me to say it back?"

Even from across the room, Sam swore he could _hear_ his brother swallow tightly.

His voice was low, rough as he replied, "Only if you mean it."

She licked her lips, head falling to the side. "If you don't know I love you... Obviously-"

Whatever quick retort she was bound to give didn't come, because Dean had leaned up and caught her lips in his, his arm wrapping around her waist and nearly picking her right up off the bed, hauling her into his lap.

Sam grinned to himself, unplugging his laptop and closing it. Obviously, he was meant to be at a diner for the next few hours, to let them enjoy their newfound love. Grabbing his jacket and pulling on his boots, he snorted to himself as he closed the door, rolling his eyes as Dean waved his hand back as if just now telling him to get lost.

He was happy for them, he really was and as the weeks, months, years went by, he was only more and more reassured that it was simply meant to be Dean and Chloe. While Dean didn't shout his love for her at every corner, he wasn't afraid to say it anymore. He didn't get all girly about it, that just wasn't his style, but he didn't pretend he didn't have those feelings, which was a large step in itself.

_"Does anything_ ever _make it to your mouth?" Chloe wondered, wiping at his chin with a napkin._

_"Love you too, sweetheart," he replied._

It was easy and lighthearted most of the time. But even when he was joking, the affection was always in his voice. Even when they were hollering at each other, arguing over this or that...

_"Dean! You're being ridiculous! What was I supposed to do? That man was going to_ die _out there if I didn't heal him!" Her chest heaved, hands on her hips, face flushed with anger._

_"Yeah, I get it, poor him." He glared darkly. "But hell, Chloe, we don't know how this thing works... If you save one life too many, you might not wake up. Now how the hell am I supposed to accept that? Huh? Tell me!" He threw his arms out expectantly._

_"This is our job! Saving people..." She shook her head. "We do it in different ways and yes, there's a consequence and I understand that it could be not waking up, but that doesn't mean I'm just going to_ stop _!"_

_"Why? Why not?" he rasped out. "We were doin' just fine before this. People die, Chloe. We can't save ‘em all." He glared at her, his shoulders tense._

_Sam stood quiet in the background, this was one subject he never interjected on. He had his opinions, but he wasn't sure it was the healing that bothered Dean so much as the dying... And he couldn't say he'd happily accept Chloe's death over some strangers... Yes, he believed that everybody deserved a chance and he'd do anything to keep someone alive, but if that meant the death of his brother or his best friend... He knew who he'd pick and it wasn't the noble choice._

_"We save as many as we can!" She stared back at him, eyes wide. "If you had this ability and it was Sam out there, wouldn't you-"_

_"It's not the same! If it was Sam, well that's my_ brother _," He made a face. "Not some guy in the wrong place."_

_"Exactly, Dean. He was just in the wrong place! Does that mean he should die for it? When I have the chance and the ability to save him?"_

_"If it means your life?" He lifted his shoulders, lips firm. "Then yeah, fuck him, let him die." He shook his head. "I'm not givin' you up just so some idiot can go on living his lame ass life, never knowing what you gave up for him, never doing anything that's really worth a damn. It's not worth it."_

_"You can't mean that." She shook her head. "You're entire life has been about saving people."_

_"If it means my family, then I will do_ everything _I possibly can to keep them safe. If that means somebody else has gotta die, then I'm sorry... I'm no saint, never said I was... So if they die and you live..." He shrugged. "Well I can't feel sorry about that."_

_"So you'd let them die... You'd let them bleed out and leave whoever it was_ they _loved and_ they _would do anything for...?" Her brow furrowed._

_He crossed the room, gripped her shoulders tight in his hands and stared at her. "I would do anything in my power to save some innocent from death... But if that same person can only live if you die..." He shook his head. "I won't do it. I won't let you do it." He licked his lips. "And you can hate me but I love you too damn much for that."_

_She shook her head, biting her lip painfully as tears filled her eyes. "You know I can't let them just die out there..."_

_"Yeah..." He nodded. "And you better believe I'm gonna try and stop you every damn time... And we're gonna have this fight every time you wake up..." He swallowed tightly. "_ If _you wake up."_

_She stared up at him before finally wrapping her arms around him tightly. "I don't_ want _to die... You have to know that."_

_He hauled her up against him and buried his face in her hair._

_Sam left then, able to slip out of the room before either could notice. He wiped his eyes discreetly before pulling out his cell phone and pressing the speed dial. "Sarah? Hey... It's Sam..."_

So he couldn't always agree that they were a match made in heaven. They had their ups and downs, they fought, they argued and on occasion he'd even had Dean push him over in the bed because Chloe kicked him out of theirs, but they always made up. She always took him back and he accepted that whatever happened, good or bad, he had her, through thick and thin. They made it through the little things; dingy motel rooms, bad diners, life on the road. They made it through the hard stuff; emotional turmoil, the time she "died" and stayed that way four days straight and Sam was readying the burning table, and even a demon war, where friends and innocent people were lost in the thousands. They made it through the birth of their son, Thad Samuel Winchester, and later their daughter, Grace Martha Winchester. They made it through the day the Impala just wouldn't start again, no matter what Dean did, and the day Bobby died, willing his house to them to raise up their family.

And forty years later, when Sam had children, grandchildren, and a great grandson on the way, with his wife Sarah at his side, Sam could still say he knew from the start to the very end that they were _it_ ; that Dean had finally found his equal, the woman that would stand next to him for the rest of their lives. He knew it before they did, had every reason under the sun. But the last one, the one that stood out most, were those three words that.She got him to say it; without pushing him or waiting with expectation. He just said it, when he was ready, and that's how they all knew he really meant it.

All the signs were there, all the reasoning came out right. She never took his crap; an entire lifetime could go by and she always knew how to deal with him. She was there to tell him if he needed to get away from hunting, if he was ever ready to stop, she'd support him. And if or when he picked the sawed off up again, she'd be there next to him then too. And even as they aged, married, had kids, Dean continued to be jealous. Not to the overwhelming point he'd once been, back when he didn't have the comfort of knowing that she was his, either way. But he had a tendency of staking his claim on her whenever any men so much as glanced in her direction. "He was cute, wasn't he?" she'd tease, patting his chest. And she never got in the way of their brotherhood. She encouraged it even when Sam moved a few states away, to live with Sarah and start his own happily ever after. He knew for a fact that Dean would come home in a foul mood some days only to find she'd packed his duffel bag, got his Zeppelin and Metallica tapes out and already called ahead to let Sarah know that he was coming. And he'd spend a weekend out with Sam, just relaxing and hanging out. Sarah would pack up her own bag and take a flight out to spend time with Chloe or sometimes visit her father. That way there were no interruptions during Sam/Dean time.

Most important of all in Sam's research project that was Chloe and Dean, was the last reason that made it all certain. It all came down to those five things that made Chloe perfect for Dean. And above all else, she got Dean, man of few honest and affectionate words, to say I love you. Whenever he felt like it or it was warranted, he'd say them. Mumble them in her hair, call it back to her teasingly whenever he did something she didn't approve of, vowed it when they got married, told her it a few million times when she had his son and daughter. And Sam knew how hard it was for Dean to say it, to admit to anything like that, but when it came to Chloe, the words came out, easy and right. Just another checkmark on the list of reasons Sam had been right all along. And his brother could bitch and complain all he wanted about how Sam was some girly romantic at heart, but in the end, he was just happy that his brother had been right... That Chloe really was the perfect woman for him. ‘Cause, really? Who else would put up with him this long?


End file.
